Triethylamine → (2,3,4-Trimethoxy-6-methylphenyl)(2,5-dichloro-3-trifluoromethyl-4-pyridyl)methanol

HRID 242429Notes

Reaction equation

HRID 242429 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[CH:13]=[C:12]([CH3:20])[C:11]=1[CH:21]([C:23]1[C:28]([C:29]([F:32])([F:31])[F:30])=[C:27]([Cl:33])[N:26]=[C:25](Cl)[C:24]=1[Cl:35])[OH:22]>CO.[C].[Pd]>[CH3:8][O:9][C:10]1[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[CH:13]=[C:12]([CH3:20])[C:11]=1[CH:21]([C:23]1[C:24]([Cl:35])=[CH:25][N:26]=[C:27]([Cl:33])[C:28]=1[C:29]([F:30])([F:32])[F:31])[OH:22]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 12151537(2,3,4-Trimethoxy-6-methylphenyl)(2,3,6-trichloro-5-trifluoromethyl-4-pyridyl)methanol

Product 1

HCID 12151535(2,3,4-Trimethoxy-6-methylphenyl)(2,5-dichloro-3-trifluoromethyl-4-pyridyl)methanolYield 24%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2.7 ml (19 mmol) of triethylamine and 0.9 g of 5% palladium carbon were added to a solution having 2,3,4-trimethoxy-6-methylphenyl)(2,3,6-trichloro-5-trifluoromethyl-4-pyridyl)methanol obtained in Step (a) dissolved in 200 ml of methanol, followed by stirring under a hydrogen atmosphere for 14 hours. The mixture was subjected to filtration, 30 ml of water was added, and methanol was distilled off under reduced pressure. After extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain 2.38 g (yield: 24%) of (2,3,4-trimethoxy-6-methylphenyl)(2,5-dichloro-3-trifluoromethyl-4-pyridyl)methanol (melting point 162 to 165° C.).

Workup

  1. filtrationThe mixture was subjected to filtration, 30 ml of water
  2. additionwas added
  3. distillationmethanol was distilled off under reduced pressure
  4. extractionAfter extraction with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. filtrationsubjected to filtration
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d4615426745248f78e6fe733cbb50c71
Source dataset
uspto-grants-2014_02
Patent number
US08653113B2

Reaction notes

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